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Acetic acid-promoted cascade N-acyliminium ion/aza-Prins cyclization: stereoselective synthesis of functionalized fused tricyclic piperidines
Uppsala University, Disciplinary Domain of Medicine and Pharmacy, Faculty of Pharmacy, Department of Medicinal Chemistry, Organic Pharmaceutical Chemistry.
Uppsala University, Disciplinary Domain of Medicine and Pharmacy, Faculty of Pharmacy, Department of Medicinal Chemistry, Organic Pharmaceutical Chemistry.
Uppsala University, Disciplinary Domain of Medicine and Pharmacy, Faculty of Pharmacy, Department of Medicinal Chemistry, Organic Pharmaceutical Chemistry.
2017 (English)In: Chemical Communications, ISSN 1359-7345, E-ISSN 1364-548X, Vol. 53, no 13, 2110-2113 p.Article in journal (Refereed) Published
Abstract [en]

A novel acetic acid-promoted metal-free cascade N-acyliminium ion/aza-Prins cyclization of o-formyl carbamates and homoallylamines is reported. This one-pot protocol provides efficient and rapid access to masked cis-hydroxyhexahydropyrido[1,2-c] quinazolin-6-ones with concomitant generation of two stereogenic centers, four C-C/C-O/C-N bonds and two new rings in good yield and excellent diastereoselectivity.

Place, publisher, year, edition, pages
ROYAL SOC CHEMISTRY , 2017. Vol. 53, no 13, 2110-2113 p.
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Medicinal Chemistry
Identifiers
URN: urn:nbn:se:uu:diva-319679DOI: 10.1039/c6cc09805cISI: 000395625700006PubMedID: 28133651OAI: oai:DiVA.org:uu-319679DiVA: diva2:1087460
Available from: 2017-04-07 Created: 2017-04-07 Last updated: 2017-04-07Bibliographically approved

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Sawant, Rajiv T.Odell, Luke R.
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